Vacation rentals in Ashland

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Top-rated vacation rentals in Ashland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Cottage in Ashland
Charming very well appointed cottage !
The Farm Cottage is a renovated former horse hotel. It retains the charm of its former use yet is well appointed and updated for comfort & convenience. The cottage overlooks a pasture with 2 barns with the Siskiyous beyond to the south & the Ashland, Grizzly Peak Hills to the east. We are only 2 easy miles from downtown Ashland with multiple wineries close by. There is hiking, swimming at Emigrant Lake nearby as well. If quiet is what you are looking for, the cottage will meet all your needs.
Dec. 31 – Jan. 7
$194 CAD per night
4.96 out of 5 average rating, 360 reviews
Guest favourite
Guesthouse in Ashland
Charming cottage, walk to town.
Our guests at The Ashland Cottage are always thrilled upon arrival, "It's gorgeous!" The cottage offers exactly what Ashland visitors are seeking: Comfort and charm, ample amenities and a walkable location. The cottage is newly constructed yet designed with the same Craftsman appeal as our 1920s residence. As a separate house with a private entrance, the cottage offers spacious living with high ceilings, natural light and inspiring views.. all within a 10 minute walk to theaters and downtown
Nov. 19 – 26
$265 CAD per night
4.97 out of 5 average rating, 427 reviews
Guest favourite
Cottage in Ashland
Victorian Garden Carriage House
You will wake in the trees, to the soft prospects of the forested Siskiyou mountains to the west. You'll discover enchanting views at every window, from city streets to a quiet English garden and pond. You are only a few steps from Ashland Plaza, yet the retreat-like environment we offer to all our guests requires that no incense, smoking, vaping or pets are allowed in the Carriage House. The City of Ashland has authorized the Carriage House. Our City Planning Action Number is PA-2013-01701.
Oct. 30 – Nov. 6
$321 CAD per night
4.97 out of 5 average rating, 419 reviews

Popular amenities for Ashland vacation rentals

Stay near Ashland's top sights

Lithia Park198 locals recommend
Oregon Shakespeare Festival267 locals recommend
Ashland Springs Hotel3 locals recommend
Ashland's Own Shop'n Kart38 locals recommend
Brickroom76 locals recommend
Ashland Food Co-op91 locals recommend

Other great vacation rentals in Ashland

Guest favourite
Cabin in Ashland
Beautiful Barndominium by Howard Prairie Lake
Jul. 26 – Aug. 2
$247 CAD per night
4.96 out of 5 average rating, 155 reviews
Guest favourite
Guesthouse in Ashland
Courtside Cottage - WalkScore 93 - Dog Friendly
Sep. 3 – 10
$373 CAD per night
4.98 out of 5 average rating, 110 reviews
Guest favourite
Guesthouse in Ashland
Comfortable, Private Guest Lodging
Apr. 25 – May 2
$179 CAD per night
4.95 out of 5 average rating, 312 reviews
Guest favourite
Treehouse in Jacksonville
Tree Top Studio
Jul. 28 – Aug. 4
$289 CAD per night
4.98 out of 5 average rating, 180 reviews
Guest favourite
Home in Ashland
Ashland Haus Retreat - 1 block from downtown!
Oct. 30 – Nov. 6
$329 CAD per night
4.91 out of 5 average rating, 190 reviews
Guest favourite
Cottage in Phoenix
The Pear Cottage Where city and country life meet
Aug. 15 – 22
$167 CAD per night
4.91 out of 5 average rating, 311 reviews
Guest favourite
Guesthouse in Ashland
Modern Airy Retreat - Views, Walk to Everything
Aug. 31 – Sep. 7
$345 CAD per night
4.94 out of 5 average rating, 117 reviews
Guest favourite
Farm stay in Ashland
Kelly’s Farm 4 miles to Ashland
Sep. 4 – 11
$256 CAD per night
4.94 out of 5 average rating, 586 reviews
Guest favourite
Home in Ashland
The Aloha House - Hot Tub - Pool
Dec. 19 – 26
$618 CAD per night
5.0 out of 5 average rating, 17 reviews
Superhost
Tiny homes in Ashland
Ashland tiny home with view and barrel sauna
May 8 – 15
$129 CAD per night
4.83 out of 5 average rating, 69 reviews
Guest favourite
Guest suite in Ashland
Summer’s Night Cottage 8 minute walk to Downtown
Apr. 2 – 9
$159 CAD per night
4.93 out of 5 average rating, 72 reviews
Guest favourite
Guesthouse in Ashland
The Poets' Inspiration Cottage
May 5 – 12
$231 CAD per night
4.95 out of 5 average rating, 38 reviews

Quick stats about vacation rentals in Ashland

Total rentals

280 properties

Rentals with dedicated workspaces

140 properties have a dedicated workspace

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

100 properties allow pets

Family-friendly rentals

100 properties are a good fit for families

Total number of reviews

19K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Oregon
  4. Jackson County
  5. Ashland